What If?
by Beckie Gloom
Summary: What if Will and Jack had gotten together when they were teenagers, and Will had never reconciled with Grace? What if Karen never married Stan? AU, set sometime in season 7. Mostly WillJack.
1. Chapter One

**Disclaimer: **I don't own any of this. But if they're interested in selling Will and/or Jack, someone let me know, okay?

**Summary: **Fans of _Friends _might recognise the basic idea for this story. What might have happened if things had gone differently in the flashbacks in 'Lows in the Mid '80s'? What if Will and Jack had gotten together when they were teenagers? What if Will and Grace never reconciled after their breakup? What if Karen never married Stan, but still had Rosario come to work for her?

**Chapter One**

The jewellery department was almost empty. Outside the cold late-autumn winds were raining red and yellow leaves against the big display windows in irregular bouts. The lone salesgirl smiled disinterestedly at Will before returning to her magazine.

Will perused the glass cases, feeling nervous and a little out-of-place. Having never been called upon to buy this kind of gift before, he was totally out of his depth.

"Excuse me?" he called to the salesgirl. She put down her magazine – managing not to look too put out – and walked around the counter over to where he was standing.

"Sir?" she asked politely. Her nametag read SALLY.

"I'm… um… looking for an engagement ring," Will said, sounding as awkward as a newly-of-age kid buying his first pack of condoms. _Come on man, you're thirty-seven, _he scolded himself.

The girl gave him a puzzled look and started her spiel. About three-quarters of the way through the elevator doors opened and deposited a flustered-looking redhead woman in a long coat and a zig-zag-patterned dress which was almost certainly a mistake. She went over to the sales counter and re-arranged her windswept hair while she waited for the girl to finish.

Eventually, when Sally had left Will equally as undecided as he had been beforehand, the woman started to speak.

"Hi, I've got a couple of things I'd like to return," she said, rummaging through her spacious handbag and depositing a couple of small display boxes on the top of the desk.

"Okay, do you have the receipts?" Sally asked, smiling that flawless, genuine smile that only very new salespeople can manage.

"Here's the thing," said the woman, and Will looked up, suddenly certain he knew her from somewhere. "They're my wedding and engagement rings from my adulterous soon-to-be-ex-husband, and if there is any way I could return them without the receipts then I'd really like to know about it, please."

Sally's brow furrowed. "I'm in a little over my head here," she said after a moment. "I'm just gonna go get my supervisor."

She swept over to the EMPLOYEES ONLY door at the back of the room and was gone.

The woman turned around and her eyes locked on Will's. "Oh, my God," she said, almost instantly, "Will Truman? Is that you?"

Will thought back desperately, searching for a name. One made itself known very quickly. "Grace?" he exclaimed.

Her face lit up in the familiar smile. "Yeah!" she squeaked, going over to him and giving him a brief hug. "Wow! Fancy meeting you here!"

Will nodded. "How long has it been?"

She thought for a moment. "Must be something like… eighteen years. Woah."

"That long?" he asked. "I thought it had only been about five or six. Are you sure?"

"Yup," she replied. "Definitely. We were nineteen the last time we spoke, remember?

"So what brings you to the Tiffany's jewellery department?"

"Well," he said, "_Hopefully _I'm about to get engaged. I've already heard what brought you here," he added, smiling slightly.

"Oh," she said, blushing, "You heard that, then?"

"Grace, the entire block heard it," he grinned, teasing her as if they'd been apart for mere days instead of nearly two decades, and as if their last meeting had ended on friendly terms.

"Okay, so my problems have been broadcast to a not inconsiderable part of Manhattan's population," she said, "But tell me all about the lucky guy."

Will reddened slightly, remembering their break-up. "Didn't forget that, then?" he asked.

"How the hell could I?" she inquired. "I was down about it for almost three years. But I'm not still mad at you, if that's what you mean. Eighteen years forgives a lot. Plus I've got a new vent for my anger towards exes – Dr. Marvin Leo I-Can-Save-The-Third-World-But-Not-My-Own-Marriage Adultery-Committing Marcus, the lying-cheating bas – so tell me all about your husband-to-be."

The abrupt change in conversation threw Will off for a moment. "Oh," he said, once what she had asked had registered. "Um… It's our seventeenth anniversary in two weeks' time and – "

"Seventeen years?" she asked. "So you've been together since you were like, twenty?"

Will nodded. "He was nearly nineteen, I was just turned twenty."

"Wow," she said, "I wish I could find that level of commitment. Although obviously it was too much to ask of a certain two-timing Red Cross Aid Worker-seducing – quit holding out on me, what's his name?"

Once again, Will took a moment to figure out what she was saying. "His name is Jack McFarland," he said. "I think you met him at a party once, when you and I were still, you know, _together_ – but you probably won't remember him."

Grace pondered on this for a moment. "The high school kid with braces and blonde streaks in his hair?" she asked after a moment. "The one at Matt Stokes's who couldn't take his eyes off of you the whole night?"

Will nodded, unable to avoid grinning. "I guess, although I hadn't noticed the last one," he admitted. "But I would like to point out the braces and blonde streaks are a fond but fortunately distant memory."

"Well, I guess a lot of things seemed like a good idea back then," she agreed. "We were kids, it was the '80s, everyone had bad hair."

Sally burst back through the Employees Only door. "I'm sorry, my supervisor is unavailable right now," she said, "But she looked at the items in question and doesn't think they can be returned very easily, especially without the receipts."

Grace rolled her eyes in annoyance.

"Sir, do you need any more help?" Sally inquired politely of Will.

"No thanks," Will replied quickly, "I'm gonna think on it for a while and come back tomorrow, if that's okay."

"Alright, sir," Sally said, and smiled.

Will and Grace made their way towards the elevator. "Wanna get lunch or something?" Grace asked.

"Sure," he replied. "I know a good place."

"Great! They don't sell carrot cake, do they?"

"I don't think so," he replied.

"Oh, thank God!" she exclaimed. "No self-respecting cake should be caught fraternising with vegetables. I refuse outright to be in the same room as the traitor cake."

Will grinned. "It really is you."

_TBC..._


	2. Chapter Two

**Disclaimer: **I still don't own anything. At least not outside of the occasional daydream.

**Chapter Two**

"So where do you work now?" Grace asked. They were sitting at a table for two in the small café Will had been frequenting ever since he started working in the area. Will was sipping coffee; Grace was demolishing a mountainous cheesecake.

"A law firm," Will replied. "Doucette & Stein. Well," he added, shifting awkwardly in his chair as if about to disclose something embarrassing, "It's looking increasingly like it's going to be Doucette, Stein & Truman by this time next year."

Grace paused with a forkful of cake halfway to her mouth. "Congratulations, Mr. Big-Shot," she said.

Will blushed slightly. "So what do you do for a living?" he asked.

"I'm an interior designer," she replied. "Grace Adler Designs. Not all that well-known, but we've got outlets in most east-coast states now."

"Wow," Will said, grinning, "The travel time you must rack up – "

Grace laughed. "I work out of the Manhattan branch," she replied. "There's only fifty employees in all, and including me there's five of us in New York. I was hoping to move to Florida to work there but, you know, my mother would probably want to come live with me, especially now my husband's out of the picture."

"Speaking of moms," Will said, "I totally forgot to ask if you have any kids."

Grace shook her head. "We were going to start trying after Leo finished up in Cambodia so he could be around for the early days," she said, "But then Leo decided the night before he left he was going to sleep with some missionary and so I was kind of put off the idea.

"Do you have any?"

Will nodded. "A teenage daughter," he replied.

"Aw, how cute!" Grace exclaimed. "What's her name?"

"Well, the thing is – Jack _is _the teenage daughter," he replied, and smiled wickedly.

"That is cruel!" Grace snorted, laughing and managing to keep the spray of crumbs away from Will's suit, at least for the most part.

Will shrugged. "Why? I have the common decency to say it to his face as well as behind his back."

This made Grace laugh even harder. She was attracting some odd looks now, but neither of them cared. It was good to be catching up again after so many years apart.

"So, seriously," she said, after she had calmed down, "Any kids?"

Will shook his head. "No," he replied, "No plans, either. For one thing, Jack doesn't really want kids, and for another…"

He trailed off.

"What?" Grace prompted.

"It's going to sound corny and more than a little crazy if I say it," Will said.

"C'mon," Grace cajoled, "Tell me. There's very little I haven't heard before. You wouldn't _believe _the secrets interior designers are in on. Affairs, kinky sexual habits, illegitimate kids… You name it, I've had a client who's done it and then told me about it."

It was Will's turn to laugh. "Nothing like that, I assure you," he said. "Okay, what I was going to say was… Although I always liked the idea of having kids, I like the idea of spending all my time just focusing on Jack even more." There was a moment's silence between them. "See, I told you it was crazy."

Grace shook her head, a look of awe on her face. "It's not crazy," she said, "My God! It's just about the most romantic thing I've ever heard!"

Will looked dubious. "Really?" he asked.

She nodded. "Yeah! Totally!"

He still looked unsure. "I've never told _anyone_ that before. Not even him. It just sounds so _weird_ when I say it out loud."

"Well," Grace said, "I don't think it's weird. I think, if anything, it shows that you're definitely ready to marry him. And I'm honoured that I'm the person you've told."

Will smiled. "Even though you turned out not to be my type, we could still have been great friends, don't you think?"

Grace paused whilst licking the crumbs from her plate. "We still could be," she said after a moment. "Why not call it an eighteen year hiatus and start over?"

Will extended his hand over the table solemnly. "Will Truman," he said.

"Grace Adler," she replied. They shook hands.

XxXxX

It was a quarter past five in the evening when Will got back to his apartment. Grace, with her previous knowledge of engagement rings, had taken him to almost a dozen different stores and finally helped him pick out something he thought Jack would approve of. Will was still pretty buzzed from the excitement of everything that had happened that day.

Jack was sitting at the kitchen table, his jacket and tie lying over the back of the chair next to the one he was occupying. The top three buttons of his shirt were undone, and he was staring intently at something on the table.

"Good day?" Will inquired, hanging his coat up on the stand by the door.

"Being a vice president is hard," Jack complained. "Tonight I have to work out which of our two lowest rated shows to cancel."

"You're vice president of Out TV, not the Fox Network," Will pointed out, going over to Jack and kissing the top of his head affectionately. "I didn't even realise that channel _had _ratings. I thought people had to watch it first."

Jack glared at him. "You're funny, Truman," he growled. "You know what? If it's so easy then why don't you decide what to do?"

"Oh, please, Jack, I've spent the entire day trying to make decisions," Will said without thinking.

Jack looked slightly puzzled. "Why?"

Will cursed himself mentally and smoothly changed the subject. "You know more about TV than I do," he said, "I'm sure whatever choice you make will be the right one."

Jack raised one eyebrow. "You're not usually this affectionate before seven p.m."

Will smiled. "I've had a good day, is all. I ran into an old pal from college."

"Male or female?" Jack asked suspiciously.

Will rolled his eyes. "Female," he said, "Not that it would have made a difference if she had been a guy. Grace Adler – remember her?"

Jack thought for a moment. "Your ex-girlfriend?" he asked after a moment. "Frizzy red hair, big feet? The one who was practically surgically attaching herself to your face at Matt Stokes's?"

Will nodded and smiled vaguely. "Don't be mean, Jackie."

Jack folded his arms sulkily. "Are you taking her side?"

Will burst out laughing. "I'm not taking sides, because there are no sides, because… Oh, who cares. I'm going to take a shower and get changed."

"Wait a minute," Jack said, "I still want your opinion on which show to keep."

"Seriously?" Will asked.

Jack nodded.

"Keep the first one," he advised.

"The lesbian one?"

Will nodded.

"What possible interest can you have in lesbians?" Jack asked. "At least heterosexual couples are halfway there. Lesbians are _way _off the mark."

Will shrugged. "The majority of your shows are about men. For a gay network, lesbians are under-represented by your programming."

"Does PC Lawyer Will ever sleep?" Jack asked him.

"Yes," Will replied. "I promise there'll be no trace of him once I've showered." He trailed a series of small kisses down the back of Jack's neck. Jack shivered slightly.

"Buy anything good?" Jack asked as Will picked up his shopping bags.

"A couple of sweaters," Will replied. "One for me to wear when we visit my mother at Thanksgiving and one for you to steal so you don't resent me taking you to visit my mother at Thanksgiving."

Jack pouted. "I can't believe you're making me visit her on our anniversary. She hates me and you know it."

"First of all," Will said, taking advantage of Jack's momentary lapse in concentration to transfer the small display box from the bag to his pocket, "It's two days after our anniversary. And second my mother does not hate you."

"Will, in seventeen years can you remember one occasion on which she's said something nice about me? Or has she ever told you that she thought you made the right decision?" Jack asked.

"No, but she's never said anything like that about Ginny or Peggy, either," Will replied. "You think they've never asked Sam and Paul those exact same questions? Mom's just not very open with the way she feels about people. She likes you just fine."

Jack shrugged and didn't say anything more.

Will went into their bedroom and hid the box among the general clutter under the bed before heading to the bathroom and taking a shower.

_TBC..._

**Author's Note: **Just so we're clear, I would like to point out that Jack's comment about lesbians in this chapter in no way reflects my own views. And, while you're here, would you review, please?


	3. Chapter Three

**Disclaimer: **I still don't own anything. If I did, do you really think I'd be sitting here writing fics instead of insuring that Will and Jack get together in the next series?

**A/N: **Sorry this took so long. I've had exams and a lot of other crap to deal with, so I haven't had much time for writing. Hopefully chapter four will be posted more quickly.

**Chapter Three**

"Will," Jack whined, displaying his best puppy-dog look, "Call my office and tell them I'm sick."

Will put down his paper and looked at his partner. "Why?"

"I don't wanna go to work today," he said. "I've got to go to a _meeting_. Can you believe that? The only reason I took this job was because I thought I'd get to sit in my office all day Googling my own name and teasing the hetero interns."

"Oh, the injustice," Will said, rolling his eyes. He finished his coffee and picked up his paper again, effectively blocking Jack. "Forget it. One meeting throughout your entire career. You'll live."

"Please," Jack whimpered, removing the newspaper from Will's hands and discarding it on the empty chair next to him, out of Will's reach. "I'll call your boss and say you're sick, too. Then we can go back to bed."

"Tempting as that sounds," Will replied, smiling in spite of himself and getting up to recover the paper, "I'm scheduled to meet a client today, a client who is _very _important, and with me up for promotion it won't look good in Ben's eyes if I fake sick." He paused on the way back to his chair and kissed the top of Jack's head, "And he'll know I'm faking. We've called each other in sick before, remember? _Way _too many times for it to be plausible any more."

Jack folded his arms sulkily. "Fine. But if I die of boredom in the meeting just remember it's your own fault you're a widow."

"And when I'm a partner in the firm you'll never have to go to work again if you don't want to," Will reminded him. He glanced at the clock and cursed under his breath. "How'd it get so late? I'd better get going."

He folded the paper – of which he'd only read one short article, thanks to Jack's frequent interruptions – and got up.

Jack followed him to the door and watched Will intently as he shrugged into his coat and picked up his briefcase. "So do I at least get to hear who this client is?"

Will suddenly grinned like a kid, "A _huge_ businessman. I'll ask how his kids are, he'll ask how my wife is, I'll remind him I'm gay for the hundredth time, we'll talk shop for an hour, I'll come home with three hundred dollars extra and a brownie point from Ben for sitting through the whole thing without falling asleep."

"Wow. And I thought my day was boring." Jack looked closely at Will. "What's so funny?"

"Remember when I said this businessman was huge? I meant literally," Will smiled.

Jack rolled his eyes. "You know, your laughter is tempting fate. You're unbalancing your karma. You'll probably wake up fat tomorrow." He thought for a second, and his eyes widened with alarm. "_I _could wake up fat tomorrow! God is hearing your fat jokes and She'll punish you by making _me _a fatty! I hope you're happy!"

It was too much. Will burst out laughing. "Then shut up, kiss me, and then let me go to work to pay for your liposuction."

Jack obeyed the first two without objection. But when Will tried to turn towards the door he hung onto his waist. "Call my boss?" he asked one final time.

Will kissed the corner of Jack's mouth. "No."

Jack abruptly let go of Will and turned away from him. "Fine. I was gonna let the liposuction comment go, but… I'm officially not talking to you. Starting from now."

"What, now as in now?" Will asked.

"Yes," Jack said, before he realised what Will had done. He turned around "Why you…" he began, then trailed off as the apartment door closed.

**X x X x X**

"Good morning, Mr. Truman."

Will looked up from his paper (with no Jack around to distract him he was actually able to read now). "Good morning, Mrs. Freeman."

Ben Doucette's secretary smiled at him in the way he'd come to know very well over the last half-decade. It was amazing how she had perfected the combination of patronisation, dislike and contempt, whilst still managing to convey the fact that she was talking to a man who would almost certainly be one of her bosses within the next twelve months.

"I brought you your coffee, and a message from Mr. Doucette," she said, placing the Styrofoam cup on his desk and never allowing that brilliantly cynical smile to leave her face. "He says that you must be serious about wanting this promotion if you're willing to spend an entire hour and a half in the company of Mr. Walker."

Will laughed slightly and picked up his coffee, nodding and smiling at Mrs. Freeman by way of thanks. "Well, please tell him that if this doesn't prove I'm serious about this promotion then nothing will."

Her false smile widened slightly. "Will do, Mr. Truman," she said, going over to the door. "Hope you have a nice day," she added before she left him alone in his office once more.

Will laughed aloud at this once he was certain she was out of earshot. "No you don't," he grinned.

The phone rang. Will answered.

"I thought you weren't talking to me," Will said by way of greeting.

"What?" The voice was familiar, but not quite familiar enough to be Jack's. "Um… I would ask if I had the right number, but… That is you, right Will?"

"Right," Will laughed. "Sorry about that. I thought you were Jack."

"Oh," Grace replied. "Ah… Is everything okay between you two?"

"Yeah, we're fine," Will said, smiling to himself slightly. "He stops talking to me at least twice a day. So what's up?"

"I was just wondering if you had lunch plans today?"

"Actually, for once I don't," Will replied. "For the first time in living memory Jack has a lunch meeting and I don't, so I'm a free man. Between twelve and one-thirty, anyway."

"Oh, great!" Grace exclaimed, obviously genuinely pleased. "Hey, how about we go back to that café we went to last week?"

"Sure," Will replied, "I'll meet you there at… Ten minutes past? Does that give you enough time to get there from your office?"

They spent another five minutes negotiating their lunch plans before saying their goodbyes and hanging up. Will was more cheerful than he usually was after doing something as every-day as making plans to meet up with a friend. Usually only finding a free lunchtime in which to meet up with Jack made him feel this content with his schedule for the day… Perhaps it was the prospect of something to look forward to after the meeting with Stanley Walker, that king of small talk, ended. Or maybe it was just Grace. It was good to be catching up with her after so many years apart. Yes, that was probably it.

**X x X x X**

"Well, this is my office," Grace said, unable to keep the pride out of her voice. "I should warn you though – three of my assistants have already gone out of state to be with their families at Thanksgiving and the one whose still here is… Well… She's a little crazy."

After finishing lunch and still with fifty minutes until Will was due back at work, the two had decided to go back to Grace's building for a while. They had discovered, to their surprise, that their respective offices were only ten minutes' walk away from each other. They had both repeatedly expressed how hard they found it to believe that they had lived and worked so close together for such a long time and yet they were only meeting up again now.

After complimenting her office, Will said, "And don't talk to me about crazy. I'm asking crazy to marry me, remember."

"I think she's probably a different kind of crazy to Jack," Grace said, "The way you describe him sound kind of 'cute' crazy, whereas she is more 'drunken' crazy. But hey – crazy is still crazy no matter what breed it is, right?"

"One of life's great lessons," Will agreed.

There was silence between them for a moment. "Wow," Grace said eventually.

"What?"

"Oh, nothing. It's just…" she paused, and laughed. "I _always _used to dream of the day we'd be picking out engagement rings together and I can honestly say I never imagined me helping you find one for another man."

Will smiled. "That is pretty trippy, isn't it?"

"Okay, here's the thing," said a voice from the doorway, "When you use the word _trippy _you sound like virgin using the word _sex_. You obviously have _no _first-hand experience in what you're talking about so my advice to you would be to just say _weird_, okay, honey? I mean, you have at least done _weird _in your time, right?"

Grace sighed and turned around. "Soon-to-be future husband of Cute Crazy, meet Drunk Crazy," she said resignedly. "Or, as they'd probably say in a normal work environment: Will Truman, meet Karen Delaney."

"Aha," Karen said, after only the most cursory glance at Will. "Grace, is this your latest excuse for a rebound guy?"

"Will and I were friends in college," Grace said patiently. "We sort of dated for a while back then. Remember I told you, we met up again last week? We've been calling each other, like, _every day _since?"

"Oh, I see, hoping to re-kindle the old flame, eh?" Karen asked, winking suggestively at Will.

"Remember I also told you we met while he was choosing an engagement ring for his partner? His _male _partner? Bringing us back to the reason why we broke up and lost touch in the first place? Any of this ring any bells, any of the voices in your head able to recall this?"

"Honey, I stopped listening to a single word you said right about the time you married Leroy."

"_Leo_."

"Who cares? All cab drivers look the same anyway."

"Leo is a _doctor_, Karen," Grace said patiently.

"If he's a doctor then why was he driving my cab?"

"He wasn't. He took the wheel of your car last Christmas when you lost control trying to open a bottle of pills and drive drunk at the same time," Grace explained.

"Well, honey, no matter who he did for a living, what it comes down to is this – Leon left you for another man. End of story."

Grace started to correct her again, but then gave up. Turning back to Will, she said, "Do you have to work with anyone this bad?"

Will nodded. "I had a meeting with a client this morning who was much worse," he said. "Have you ever heard of Walker Inc?"

"Have I ever heard of Walker Inc?" Karen screeched suddenly. Will instinctively put his hands over his ears, amazed that he had met someone whose voice could become shriller than Jack's. "Why, that bastard Stanley Walker is the reason I'm poor!"

"Karen," Grace said reasonably, "You have a penthouse apartment, a live-in maid and a new car every six months. Most people wouldn't consider you poor."

"Yeah, but if I'd stuck around long enough to marry him I could've had a three-storey house, a staff of fifty and a helicopter to go with that new car!" Karen exclaimed.

"How is that his fault?" Will asked.

"Well, it's not _my_ fault that his bitch wife wouldn't agree to a divorce for ten years after he met me! And it's not _my _fault he didn't get in touch with the hit man I recommended! Who sticks around for ten years waiting to get married?"

"I've stuck around for almost twice as long…" Will muttered under his breath. Karen didn't hear.

"And then in 1995 when she _finally _decided to grant him the divorce, I told him that if he wasn't man enough to leave his wife without her permission then he wasn't man enough to handle me! But now he makes millions of dollars a second while I'm stuck living in poverty…"

Will turned back to Grace. "Want to come over to mine for dinner tomorrow night? I'm dying to introduce you to Jack."

She smiled. "That sounds great," she said, "What time?"

"Seven?"

"Great."

He hugged her goodbye and left her office. Even out in the stairwell he could hear Karen's voice – she had continued to talk to herself long after Will and Grace stopped listening. He grinned, hoping the sound waves didn't interfere with the building's electrical system.


End file.
